Pyridyl sulphonyl ureas as herbicides and plant growth regulators

ABSTRACT

##STR1## Compounds of formula (I), where R 1 , R 2 , n, W, R 3  and A are as defined in claim 1, are suitable for use as herbicides and plant growth regulators. They can be produced by a process similar to known processes. To produce them, new compounds of formula (II) are reacted with a carbamate of formula 
     
         R*--O--CO--NR.sup.3 A, 
    
     where R 3  stands for phenyl or alkyl. 
     The compounds of formula (II) can be obtained from the corresponding sulphochlorides.

This application is a continuation of application Ser. No. 08/108,896,filed Aug. 18, 1993, now abandoned which in turn is a divisional ofapplication Ser. No. 07/859,513, filed Jun. 8, 1992 pending.

It is known that some 2-pyridylsulfonylureas have herbicidal and plantgrowth-regulating properties; cf. EP-A-13,480, EP-A-272,855,EP-A-84,224, U.S. Pat. No. 4,421,550, EP-A-103,543 (U.S. Pat. No.4,579,583), U.S. Pat. No. 4,487,626, EP-A-125,864, WO 88/04297.

It has now been found that 2-pyridylsulfonylureas having specificradicals in the 3-position of the pyridyl radical are particularlyhighly suitable as herbicides and growth regulators.

The present invention relates to compounds of the formula (I) or theirsalts ##STR2## in which R¹ is --OSO₂ NR⁴ R⁵, --NR⁶ R⁷ or iodine,

R² is H, (C₁ -C₄)alkyl, preferably (C₁ -C₃)alkyl, (C₁ --C₃)haloalkyl,halogen, NO₂, CN, (C₁ -C₃)alkoxy, (C₁ -C₃)haloalkoxy, (C₁ -C₃)alkylthio,(C₁ -C₃)alkoxy-(C₁ -C₃)alkyl, (C₁ -C₃)alkoxycarbonyl, (C₁-C₃)alkylamino, di-[(C₁ -C₃)alkyl]amino, (C₁ -C₃)alkylsulfinyl, (C₁-C₃)alkylsulfonyl, SO₂ NR^(a) R^(b) or C(O)NR^(a) R^(b)), R^(a))andR^(b))independently of one another are H, (C₁ -C₃)alkyl, (C₃-C₄)alkenyl, propargyl, or together are -(CH₂)₄ --, --(CH₂)₅ --]or --CH₂CH₂ OCH₂ CH₂ --,

R³ is H or CH₃,

R⁴ is H, (C₃ -C₄)alkyl)(C₁ -C₃)alkenyl, (C₁ -C₃)alkoxy or (C₃--C₄)alkynyl, preferably propargyl, and

R⁵ is H, (C₁ -C₃)alkyl, (C₁ -C₄)alkenyl or (C₁ -C₄)alkynyl, preferablypropargyl, or

R⁴ and R⁵ together are --(CH₂)₄ --, --(CH₂)₅ -- or --CH₂ CH₂ OCH₂ CH₂--,

⁶ is H, (C₁ -Cs)alkyl, which is unsubstituted or substituted by one ormore radicals from the group comprising halogen, (C₁ -C₄)alkoxy, (C₁-C₄)alkylthio, (C₁ -C₄)alkylsulfinyl, (C₁ -C₄)alkylsulfonyl, (C₁ -C₄-alkoxy) carbonyl and CN, (C₃ -C₆)alkenyl which is unsubstituted orsubstituted by one or more halogen atoms, (C₃ --C₆)alkynyl which isunsubstituted or substituted by one or more halogen atoms, (C₁-C₄)alkylsulfonyl which is unsubstituted or substituted by one or morehalogen atoms, phenylsulfonyl where the phenyl radical is unsubstitutedor substituted by one or more radicals from the group comprisinghalogen, (C₁ -C₄)alkyl and (C₁ -C₄)alkoxy, (C₁ -C₄)alkoxy or (C₁ -C₄-alkyl )carbonyl which is unsubstituted or substituted by one or morehalogen atoms,

R⁷ (C₁ -C₄)alkylsulfonyl which is unsubstituted or substituted by one ormore halogen atoms, phenylsulfonyl where the phenyl radical isunsubstituted or substituted by one or more radicals from the groupcomprising halogen, (C₁ -C₄)alkyl and (C₁ -C₄)alkoxy, or di-[(C₁-C₄)alkyl]aminosulfonyl or

R⁶ and R⁷ together are a chain of the formula --(CH₂)_(m) --SO₂ --,where the chain can additionally be substituted by 1 to 4 (C₁ -C₃)alkylradicals and m is 3 or 4,

n is zero or 1,

W is O or S,

A is a radical of the formula ##STR3## X is H, halogen, (C₁ -C₃)alkyl,(C₁ -C₃)alkoxy, where the two last-mentioned radicals are unsubstitutedor monosubstituted or polysubstituted by halogen or monosubstituted by(C₁ -C₃)alkoxy,

Y is H, (C₁ -C₄)alkyl, (C₁ -C₃)alkoxy or (C₁ -C₃)alkylthio, where theabovementioned alkyl-containing radicals are unsubstituted ormonosubstituted or polysubstituted by halogen. or monosubstituted ordisubstituted by (C₁ -C₃)alkoxy or (C₁ -C₃)alkylthio, and also a radicalof the formula NRsR⁹, (C₃ -C₆)cycloalkyl, (C₂ -C₄)alkenyl, (C₂-C₄)alkynyl, (C₃ -C₄)alkenyloxy or (C₃ -C₄)alkynyloxy,

Z is CH or N,

R⁸ and R⁹ independently of one another are H, (C₁ -C₃)alkyl or (C₃--C₄)alkenyl,

X¹ is CH₃), OCH₃, OC₂ H₅ )or OCF₂ H,

Y¹ is --O-- or --CH₂ --,

X² is CH₃ C₂ H₅ or CH₂ CF₃,

Y² is OCH₃, OC₂ H₅, SCH₅, SC₂ H₅, CH₃ or C₂ H₅,

X³ is CH₃ or OCH₃,

Y³ is H or CH₃,

X⁴ is CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃ or Cl,

Y⁴ is CH₃, OCH₃, OC₂ H₅ or Cl,

Y⁵ is CH₃, C₂ H₅, OCH₃ or Cl.

In the formula (I), alkyl, alkoxy, haloalkyl, alkylamino and alkylthioradicals and the corresponding unsaturated and/or substituted radicalscan in each case be straight-chain or branched. Alkyl radicals, also incombined meanings such as alkoxy, haloalkyl etc., are methyl, ethyl, n-or i-propyl, alkenyl and alkynyl radicals have the meaning of thepossible unsaturated radicals corresponding to the alkyl radicals, suchas 2-propenyl, 2- or 3-butenyl, 2-propynyl, 2- or 3-butynyl. Halogen isfluorine, chlorine, bromine or iodine.

The compounds of the formula (I) can form salts in which the hydrogen ofthe --SO₂ --NH group is replaced by a cation which is suitable foragricultural purposes. These salts are, for example, metal salts, inparticular alkali metal or alkaline earth metal salts, or alternativelyanunonium salts or salts with organic amines. Salt formation can alsotake place by addition of a strong acid to the pyridine moiety of thecompound of the formula (I). Suitable acids for this are HCl, HBr, H₂SO₄ or HNO₃.

Preferred compounds of the formula (I) or their salts are those in whichn=zero, W=O and A is a radical of the formula ##STR4## in which X, Y andZ are defined as described above.

Preferred compounds of the formula I or their salts are also those inwhich

R², R⁴, R^(b), W and A are as defined above and

R⁴ and R⁵ independently of one another are (C₁ -C₃)alkyl, allyl orpropargyl or

R⁴ and R⁵ together are --(CH₂)--, --(CH₂)₅ -- or --CH₂ CH₂ OCH₂ CH₂ --,

R⁶ is H, (C₁ -C₄)alkyl which is unsubstituted or substituted by one ormore halogen atoms or by a radical from the group comprising (C₁-C₄)alkoxy, (C₁ -C₃)alkylthio, (C₁ -C₄)alkylsulfonyl, (C_(C)₄)alkoxycarbonyl and CN, (C₁ -C₃)alkenyl, (C₁ -C₄)alkyl, (C₁-C₃)alklysulfonyl, phenylsulfonyl, phenylsulfonyl which is substitutedby one to three radicals from the group comprising halogen, (C₁-C₄)alkyl and (C₁ -C₄)alkoxy, (C₁ -C₄)alkoxy or (C₁ -C₄)alkylcarbonyl,

R⁷ (C₁ -C₄)alkylsulfonyl, phenylsulfonyl or phenylsulfonyl which issubstituted by 1, to 3 radicals from the group comprising halogen, (C₁-C₄)alkyl and (C₁ -C₃)alkoxy, or di-(C₁ -C₄ -alkyl)-aminosulfonyl or

R⁶ and R⁷ together are a chain of the formula --(CH₂)_(m) SO₂ -- where mis 3 or 4.

Particularly preferred compounds of the formula (I) or their salts arethose in which R² is H, (C₁ -C₃)alkyl, (C₁ -C₃)alkoxy, halogen or (C₁-C₃)alkylthio, R⁴ and R⁵ independently of one another are (C₁ -C₃)alkyl,R⁶ is hydrogen, (C₁ -C₄)alkyl or (C₁ -C₃)alkylsulfonyl, R⁷ is (C₁-C₃)alkylsulfonyl and A is a radical of the formula ##STR5## in which Zis CH or N, X is halogen, (C₁ -C₂)alkyl, (C₁ -C₂)alkoxy, OCF₂ H, CF₃ orOCH₂ CF₃ and Y is (C₁ -C₂)alkyl, (C₁ -C₂)alkoxy or OCF₂ H, and inparticular the compounds defined above in which n=zero and W is anoxygen atom.

The present invention further relates to processes for the preparationof the compounds of the formula (I) or their salts, which comprise

(a) reacting a compound of the formula (II) ##STR6## with a heterocycliccarbamate of the formula (III) ##STR7## in which R* is phenyl or (C₁-C₄)alkyl, or (b) reacting a pyridylsulfonylcarbamate of the formula(IV) ##STR8## with an aminoheterocycle of the formula (V) ##STR9## or(c) reacting a sulfonyl isocyanate of the formula (VI) ##STR10## with anaminoheterocycle of the formula R³ --NH--A (V) or (d) first reacting anaminoheterocycle of the formula R³ --NH--A (V) in a one-pot reactionwith phosgene in the presence of a base, such as, for example,triethylamine, and reacting the intermediate formed with apyridinesulfonamide of the formula (II) (for example analogously toEP-A-232,067).

The reaction of the compounds of the formulae (II) and (III) ispreferably carried out under base catalysis in an inert organic solvent,such as, for example, dichloromethane, acetonitrile, dioxane or THF attemperatures between 0° C. and the boiling point of the solvent.1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) or trimethylaluminum ortriethylaluminum is preferably used as the base.

The sulfonamides (II) are novel compounds. The invention also relates tothem and their preparation. They are obtained starting from suitablysubstituted 2-halopyridines, which are reacted with S-nucleophiles suchas, for example, benzylmercaptan or thiourea. The compounds formed inthis way are converted with sodium hypochlorite or chlorine into thesulfochlorides (analogously to EP-A-272,855), which are then eitherreacted directly with ammonia or with tert.-butylamine via thetert.butylamides with subsequent protective group removal to give thesulfonamides of the formula (II).

The carbamates of the formula (III) can be prepared by methods which aredescribed in South African patent applications 82/5671 and 82/5045, orEP-A-70804 (U.S. Pat. No. 4,480,101) or RD 275056.

The reaction of the compounds (IV) with the aminoheterocycles (V) ispreferably carried out in inert aprotic solvents such as, for example,dioxane, acetonitrile or tetrahydrofuran at temperatures between 0° C.and the boiling point of the solvent. The starting materials (V)required are known from the literature or can be prepared by processeswhich are known from the literature. The pyridylsulfonylcarbamates ofthe formula (IV) are obtained analogously to EP-A-44,808 orEP-A-237,292.

The pyridylsulfonylisocyanates of the formula (VI) can be preparedanalogously to EP-A-184,385 and reacted with the aminoheterocycles (V).

The salts of the compounds of the formula (I) are preferably prepared ininert solvents such as, for example, water, methanol or acetone attemperatures of 0°-100° C. Suitable bases for the preparation of thesalts according to the invention are, for example, alkali metalcarbonates, such as potassium carbonate, alkali metal and alkaline earthmetal hydroxides, ammonia or ethanolamine. HCl, HBr, H₂ SO₄ or HNO₃ areparticularly suitable as acids for salt formation.

By `inert solvents` in the process variants above, solvents are in eachcase meant which are inert under the particular reaction conditions, butwhich do not have to be inert under all reaction conditions.

The compounds of the formula (I) according to the invention have anexcellent herbicidal activity against a broad spectrum of economicallyimportant monocotyledon and dicotyledon weeds. Even perennial weeds,which are difficult to control and shoot from rhizomes, root stocks orother perennial organs, are well controlled by the active compounds. Itis irrelevant here whether the substances are applied pre-sowing,pre-emergence or postemergence. In particular, some representatives ofthe monocotyledon and dicotyledon weed flora which can be controlled bythe compounds according to the invention may be mentioned by way ofexample without a restriction to certain species being intended by theirmention.

On the monocotyledon weed species side, for example, Avena, Lolium,Alopecurus, Phalaris, Echinochloa, Digitaria, Setaria and Cyperusspecies from the annual group and on the perennial species sideAgropyron, Cynodon, Imperata and Sorghum and also perennial Cyperusspecies are well controlled.

In the case of dicotyledon weed species, the spectrum of action extendsto species such as, for example, Galium, Viola, Veronica, Lamium,Stellaria, Amaranthus, Sinapis, Ipomoea, Matricaria, Abutilon and Sidaon the annual side and Convolvulus, Cirsium, Rumex and Artemisia in thecase of the perennial weeds.

Under the specific cultivation conditions, weeds occurring in rice, suchas, for example, Sagittaria, Alisma, Eleocharis, Scirpus and Cyperus arealso outstandingly controlled by the active compounds according to theinvention.

If the compounds according to the invention are applied to the surfaceof the soil before germination, the emergence of the weed seedlings iseither completely prevented or the weeds grow to the seed leaf stage,but then cease their growth and finally die completely after the passageof three to four weeks.

On application of the active compounds to the green parts of plantspost-emergence, a drastic stop to growth also occurs very rapidly afterthe treatment and the weed plants remain at the growth stage present atthe time of application or die completely after a certain time, so thatin this manner weed competition which is damaging for the crop plants iseliminated very early and in a lasting manner.

Although the compounds according to the invention have an excellentherbicidal activity against monocotyledon and dicotyledon weeds, cropplants of economically important crops such as, for example, wheat,barley, rye, rice, corn, sugarbeet, cotton and soya are only damagedinsubstantially or not at all. For these reasons, the present compoundsare very highly suitable for selectively controlling undesired plantgrowth in agricultural productive plantings.

Moreover, the substances according to the invention show excellentgrowth regulatory properties in crop plants. They intervene in aregulating manner in the plant's own metabolism and can thus be employedfor influencing plant contents in a controlled manner and forsimplifying harvesting such as, for example, by causing desiccation andstunting of growth. In addition, they are also suitable for the generalcontrol and inhibition of undesired vegetative growth without killingthe plants. In many monocotyledon and dicotyledon crops, inhibition ofthe vegetative growth plays a great role, as lodging can be reduced bythis or completely prevented.

The compounds according to the invention can be used in the customarypreparations in the form of wettable powders, emulsifiable concentrates,sprayable solutions, dusting agents or granules. The invention thereforealso relates to herbicidal and plant growth-regulating agents whichcontain compounds of the formula (I) or their salts.

The compounds of the formula (I) can be formulated in various ways,depending on which biological and/or physicochemical parameters aregiven. Examples of suitable formulation possibilities are: wettablepowders (WP), water-soluble powders (SP), water-soluble concentrates,emulsifiable concentrates (EC), emulsions (EW), such. as oil-in-waterand water-in-oil emulsions, sprayable solutions, suspension concentrates(SC), dispersions based on oil or water, oil-miscible solutions, capsulesuspensions (CS), dusting agents (DP), seed dressings, granules forbroadcasting and application to the soil, granules (GR) in the form ofmicrogranules, sprayable granules, swellable granules and adsorptiongranules, water-dispersible granules (WG), water-soluble granules (SG),ULV formulations, microcapsules and waxes.

These individual formulation types are known in principle and aredescribed, for example, in: Winnacker-Kuchler, "Chemische Technologie",volume 7, C. Hauser Verlag Munich, 4th Edition 1986; Wade vanValkenburg, "Pesticide Formulations", Marcel Dekker N.Y., 1973; K.Martens, "Spray Drying Handbook", 3rd Ed. 1979, G. Goodwin Ltd. London.

The necessary formulation auxiliaries such as inert materials,surfactants, solvents and other additives are also known and aredescribed, for example, in: Watkins, "Handbook of Insecticide DustDiluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J.; H.v.Olphen, "Introduction to Clay Colloid Chemistry"; 2nd Ed., J. Wiley andSons, N.Y.; C. Marsden, "Solvents Guide", 2nd Ed., Interscience, N.Y.1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp.,Ridgewood N.J.; Sisley and Wood, "Encyclopedia of Surface ActiveAgents", Chem. Publ. Co. Inc., N.Y. 1964; Schonfeldt,"Grenzflachenaktive Athylenoxidaddukte" (Surface-active ethylene oxideadducts), Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Kuchler,"Chemische Technologie" (Chemical Technology), Vol. 7, C. Hauser VerlagMunich, 4th Edition, 1986.

Combinations with other pesticidally active substances, fertilizersand/or growth regulators can also be prepared based on theseformulations, for example in the form of a finished formulation or as atank mix.

Wettable powders are preparations which can be dispersed uniformly inwater which apart from the active compound and in addition to a diluentor inert substance also contain wetting agents, for examplepolyoxyethylated alkylphenols, polyoxyethylated fatty alcohols and fattyamines, fatty alcohol polyglycol ether sulfates, alkane sulfonates oralkylbenzenesulfonates and dispersants, for example sodiumligninsulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodiumdibutylnaphthalenesulfonate or alternatively sodibm oleylmethyltaurate.

Emulsifiable concentrates are prepared by dissolving the active compoundin an organic solvent, for example butanol, cyclohexanone,dimethylformamide, rylene or alternatively high-boiling aromatics orhydrocarbons with the addition of one or more emulsifiers. Examples ofemulsifiers which can be used are: calcium alk-ylarylsulfonates such asCa dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acidpolyglycol esters, alk-ylary. polyglycol ethers, fatty alcoholpolyglycol ethers, propylene oxide-ethylene oxide condensation products,alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitanfatty acid esters, polyoxyethylene sorbitol esters.

Dusting agents are obtained by grinding the active compound with finelydivided solid substances, for example talc, natural clays such askaolin, bentonire and pyrophyllite, or diatomaceous earth.

Granules can be prepared either by spraying the active compound ontoadsorptive, granulated inert material or by applying active compoundconcentrates by means of adhesives, for example polyvinyl alcohol,sodium polyacrylate or alternatively mineral oils, to the surface ofcarriers such as sand, kaolinires or granulated inert material. Suitableactive compounds can also be granulated in the manner customary in thepreparation of fertilizer granules, if desired mixed with fertilizergranules.

The agrochemical preparations as a rule contain 0.1 to 99 percent byweight, in particular 0.1 to 95% by weight, of active compound of theformula (I).

In wettable powders the active compound concentration is, for example,about 10 to 90% by weight, the remainder to 100% by weight is composedof customary formulation components. In emulsifiable concentrates, theactive compound concentration can be about 1 to 85% by weight, usually 5to 80% by weight. Pulverulent formulations contain about 1 to 25% byweight, usually 5 to 20% by weight of active compound, sprayablesolutions about 0.2 to 20% by weight, usually 2 to 20% by weight ofactive compound. In the case of granules, the active compound content insome cases depends on whether the active compound is liquid or solid. Asa rule, the content in the water-dispersible granules is between 10 and90% by weight.

In addition, said active compound formulations optionally contain theadhesives, wetting agents, dispersants, emulsifiers, penerrants,solvents, fillers or carriers customary in each case.

For application, the formulations in commercially available form areoptionally diluted in a customary manner, for example by means of waterin the case of wettable powders, emulsifiable concentrates, dispersionsand water-dispersible granules. Pulverulent preparations, granules forapplication to the soil or broadcasting and sprayable solutions arecustomarily not diluted further with other inert substances beforeapplication.

The required application rate of the compounds of the formula (I)varies, inter alia, with the external conditions such as temperature,humidity and the nature of the herbicide used. It can vary within widelimits, for example between 0.001 and 10.0 kg/ha or more of activesubstance, but it is preferably between 0.005 and 5 kg/ha.

Mixtures or mixed formulations with other active compounds, such as, forexample, insecticides, acaricides, herbicides, safeners, fertilizers,grow-oh regulators or fungicides are also optionally possible.

A. CHEMICAL EXAMPLES Example 1 2-Benzylthio-3-iodopyridine

A solution of 34.0 g (0.15 mol) of 2-fluoro-3-iodopyridine and 18.6 g(0.15 mol) of benzylmercaptan in 250 ml of acetonitrile is heated underreflux with 22.8 g (0.165 mol) of potassium carbonate for 8 h. Themixture is cooled, the solvent is removed on a rotary evaporator, theresidue is taken up in dichloromethane and the organic phase is washedwith water. After drying with sodium sulfate, evaporating and distillingthe oily residue in vacuo, 37.3 g (76% of theory) of2-benzylthio-3-iodopyridine of boiling point 150°-153° C. at 0.1 mbarare obtained.

Example 2 3-Iodo-2-pyridinesulfonamide

510 ml (0.34 mol) of a 5% strength sodium hypochlorite solution areadded dropwise at 0° C. to a mixture of 25.0 g (76.5 mmol) of2-benzylthio-3-iodopyridine, 125 ml of dichloromethane, 60 ml of waterand 38 ml of concentrated hydrochloric acid. The mixture is stirred at0° C. for 30 min, extracted 3× using 100 ml of dichloromethane each timeand the organic phase is dried using sodium sulfate. The solution thusobtained is cooled to -20° C. 6.8 g (0.4 mol) of ammonia is passed in atthis temperature in the course of 20 min, and the mixture is stirred at-20° C. for 2 h and allowed to come to room temperature. The reactionmixture is washed with water and the organic phase is dried andevaporated. Trituration of the residue with diisopropyl ether gives 15.5g (71% of theory) of 3-iodo-2-pyridinesulfonamide of melting point247°-250° C. (dec.)

Example 3 3-(4,6-Dimethoxypyrimidin-2-yl)-1-(3-iodo-2-pyridylsulfonyl)urea

1.2 g (0.081 mol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) are addedto a suspension of 2.1 g (7.4 mmol) of 3-iodo-2-pyridinesulfonamide and2.2 g (8.1 mmol ) of N-(4,6-dimethoxypyrimidine-2-yl)phenyl carbamate in30 ml of ace=onitrile. The resulting solution is stirred at roomtemperature for 45 min and 20 ml of water are then added. The mixture isacidified to pH 4 using hydrochloric acid and the precipitated productis filtered off with suction. 3.2 g (93% of theory) of3-(4,6-dimethoxypyrimidin-2-yl)-1-(3-iodo-2-pyridylsulfonyl) urea ofmelting point 161°-162° C. (dec. ) are obtained.

Example 4 3-Dimethylsulfamoyloxy-2-pyridinesulfonamide

107 ml (72 mmol) of a 5% strong-oh sodium hypochlorite solution areadded dropwise at 0° C. to a mixture of 5.7 g (17.6 mmol) of2-benzylthio-3-dimethylsulfamoyloxypyridine, 30 ml of dichlorome=hane,15ml of water and 8.5 ml of concentrated hydrochloric acid. The mixture isstirred at 0° C. for 30 min, extracted 3× using 20 ml of dichloromethaneeach time and the organic phase is dried using sodium sulfate. Thesolution thus obtained is cooled to -70° C. Ammonia is passed in at thistemperature until the reaction mixture gives a distinctly alkalinereaction. After stirring at -70° C. for 3 hours, the mixture is allowedto come to room temperature and is washed with water. The organic phaseis dried and evaporated. 3.0 g (61% of theory) of3-dimethylsulfamoyloxy-2-pyridinesulfonamide are obtained;

NMR (CDCl₃): δ (ppm)=3.06 (s, 6H, N(CH₃)₂) , 5.80 (s, 2H, NH₂), 7.48(dd, 1H), 7.98 (dd, 1H), 8.38 (dd, 1H).

Example 53-(4,6-Dimethoxypyrimidin-2-yl)-1-(3-dimethylsulfamoyloxy-2-pyridylsulfonyl)urea

1.9 g (12.7 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) are addedto a suspension of 3.0 [lacuna] (10.6 mmol) of3-dimethylsulfamoyloxy-2-pyridinesulfonamide and 3.4 g (12.7 mmol) ofN-(4,6-dimethoxypyrimidin-2-yl) phenyl carbamate in 40 ml ofacetonitrile. The resulting solution is stirred at room temperature for1 h and 30 ml o f water are then added. The mixture is acidified to pH 4using hydrochloric acid and the precipitated product is filtered offwith suction. After triturating with diethyl ether, 2.1 g (42% oftheory) of3-(4,6-dimethoxypyrimidin-2-yl)-1-(3-dimethylsulfamoyloxy-2-pyridylsulfonyl)urea of melting point 155°-157° C. are obtained.

Example 63-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-1-(3-iodo-2-pyridylsulfonyl)urea

9.0 ml (18 mmol) of a 2M solution of trimethylaluminum in toluene areadded dropwise at room temperature to 4.3 g (15 mmol) of3-iodo-2-pyridinesulfonamide in 150 ml of dichloromethane. Afterevolution of gas has ceased, 3.85 [lacuna] (18 mmol) of methyl4,6-dimethoxy-1,3,5-triazin-2-yl-carbamate in 20 ml of dichloromethaneis added dropwise and the resulting solution is refluxed for 24 hours.The mixture is cooled and poured into 150 ml of ice-cold 1N hydrochloricacid. The organic phase is separated off and the aqueous phase isextractd 2× using dichloromethane. The organic phase is dried andevaporated. After triturating the crude product with diethyl ether, 3.1g (44% of theory) of3-(4,6-dimethoxy-1,3,5-triazin-2-yl)-1-(3-iodo-2-pyridylsulfonyl)urea ofmelting point 155 ° C. (dec.) are obtained.

The compounds in the following Tables 1 to 4 are obtained analogously tothe processes of Examples 1-6.

                                      TABLE 1    __________________________________________________________________________     ##STR11##    Cpd. No.           R.sup.1     R.sup.2 R.sup.3                                     X      Y       Z     M.p.    __________________________________________________________________________                                                          [°C.]    1      I           H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    161-162 (D.)    2      "           H       CH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    3      "           H       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    4      "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    186 (D.)    5      "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    177-178    6      "           H       H     CH.sub.3                                            CH.sub.3                                                    N    7      "           H       H     OCH.sub.3                                            CH.sub.3                                                    N     156-157 (dec.)    8      "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N     155 (dec.)    9      "           H       H     OCH.sub.3                                            Cl      CH    10     "           H       H     OCF.sub.2 H                                            CH.sub.3                                                    CH    11     "           H       H     OCF.sub.2 H                                            OCF.sub.2 H                                                    CH    12     "           H       H     OCH.sub.3                                            Br      CH    13     "           H       H     OCH.sub.3                                            OC.sub.2 H.sub.5                                                    CH    14     "           H       H     OCH.sub.3                                            SCH.sub.3                                                    CH    15     "           H       H     OCH.sub.3                                            OC.sub.2 H.sub.5                                                    N    16     "           H       H     OCH.sub.3                                            OC.sub.3 H.sub.7                                                    CH    17     "           H       H     OCH.sub.3                                            Cl      N    18     "           H       H     Cl     OC.sub.2 H.sub.5                                                    CH    19     "           H       H     OC.sub.2 H.sub.5                                            OC.sub.2 H.sub.5                                                    CH    20     "           H       H     C.sub.2 H.sub.5                                            OCH.sub.3                                                    CH    21     "           H       H     CF.sub.3                                            OCH.sub.3                                                    CH    22     "           H       H     OCH.sub.2 CF.sub.3                                            CH.sub.3                                                    CH    23     "           H       H     OCH.sub.2 CF.sub.3                                            OCH.sub.3                                                    CH    24     "           H       H     OCH.sub.2 CF.sub.3                                            OCH.sub.2 CF.sub.3                                                    CH    25     "           H       H     OCH.sub.2 CF.sub.3                                            OCH.sub.3                                                    N    26     "           H       H     OCH.sub.3                                            CH(OCH.sub.3).sub.2                                                    CH    27     "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    28     "           "       H     OCH.sub.3                                            CH.sub.3                                                    CH    29     "           "       H     OCH.sub.3                                            Cl      CH    30     "           "       H     CH.sub.3                                            CH.sub.3                                                    CH    31     "           "       H     OCH.sub.3                                            OCH.sub.3                                                    N    32     "           "       H     OCH.sub.3                                            CH.sub.3                                                    N    33     "           "       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    34     "           "       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    35     "           5-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    36     "           "       H     OCH.sub.3                                            CH.sub.3                                                    CH    37     "           "       H     OCH.sub.3                                            Cl      CH    38     "           "       H     CH.sub.3                                            CH.sub.3                                                    CH    39     "           "       H     OCH.sub.3                                            OCH.sub.3                                                    N    40     "           "       H     OCH.sub.3                                            CH.sub.3                                                    N    41     "           "       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    42     "           "       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    43     "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    44     "           "       H     OCH.sub.3                                            CH.sub.3                                                    CH    45     "           "       H     OCH.sub.3                                            Cl      CH    46     "           "       H     CH.sub.3                                            CH.sub.3                                                    CH    47     "           "       H     OCH.sub.3                                            OCH.sub.3                                                    N    48     "           "       H     OCH.sub.3                                            CH.sub.3                                                    N    49     "           "       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    50     "           "       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    51     "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    52     "           "       H     OCH.sub.3                                            CH.sub.3                                                    CH    53     "           "       H     OCH.sub.3                                            Cl      CH    54     "           "       H     CH.sub.3                                            CH.sub.3                                                    CH    55     "           "       H     OCH.sub.3                                            OCH.sub.3                                                    N    56     "           "       H     OCH.sub.3                                            CH.sub.3                                                    N    57     "           "       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    58     "           "       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    59     "           5-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    60     "           "       H     OCH.sub.3                                            CH.sub.3                                                    CH    61     "           "       H     OCH.sub.3                                            Cl      CH    62     "           "       H     CH.sub.3                                            CH.sub.3                                                    CH    63     "           "       H     OCH.sub.3                                            OCH.sub.3                                                    N    64     "           "       H     OCH.sub.3                                            CH.sub.3                                                    N    65     "           "       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    66     "           "       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    67     "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    68     "           "       H     OCH.sub.3                                            CH.sub.3                                                    CH    69     "           "       H     OCH.sub.3                                            Cl      CH    70     "           "       H     CH.sub.3                                            CH.sub.3                                                    CH    71     "           "       H     OCH.sub.3                                            OCH.sub.3                                                    N    72     "           "       H     OCH.sub.3                                            CH.sub.3                                                    N    73     "           "       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    74     "           "       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    75     "           4-CF.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    76     "           "       H     OCH.sub.3                                            CH.sub.3                                                    CH    77     "           "       H     OCH.sub.3                                            Cl      CH    78     "           "       H     CH.sub.3                                            CH.sub.3                                                    CH    79     "           "       H     OCH.sub.3                                            OCH.sub.3                                                    N    80     "           "       H     OCH.sub.3                                            CH.sub.3                                                    N    81     "           4-F     H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    82     "           "       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    83     "           5-CF.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    84     "           "       H     OCH.sub.3                                            CH.sub.3                                                    CH    85     "           "       H     OCH.sub.3                                            Cl      CH    86     "           "       H     CH.sub.3                                            CH.sub.3                                                    CH    87     "           "       H     OCH.sub.3                                            OCH.sub.3                                                    N    88     "           "       H     OCH.sub.3                                            CH.sub.3                                                    N    89     "           5-F     H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    90     "           "       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    91     "           6-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    92     "           "       H     OCH.sub.3                                            CH.sub.3                                                    CH    93     "           "       H     OCH.sub.3                                            Cl      CH    94     "           "       H     CH.sub.3                                            CH.sub.3                                                    CH    95     "           "       H     OCH.sub.3                                            OCH.sub.3                                                    N    96     "           "       H     OCH.sub.3                                            CH.sub.3                                                    N    97     "           "       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    98     "           "       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    99     "           4-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    100    "           "       H     OCH.sub.3                                            CH.sub.3                                                    CH    101    "           "       H     OCH.sub.3                                            Cl      CH    102    "           "       H     CH.sub.3                                            CH.sub.3                                                    CH    103    "           "       H     OCH.sub.3                                            OCH.sub.3                                                    N    104    "           "       H     OCH.sub.3                                            CH.sub.3                                                    N    105    "           "       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    106    "           "       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    107    "           5-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    108    "           "       H     OCH.sub.3                                            CH.sub.3                                                    CH    109    "           "       H     OCH.sub.3                                            Cl      CH    110    "           "       H     CH.sub.3                                            CH.sub.3                                                    CH    111    "           "       H     OCH.sub.3                                            OCH.sub.3                                                    N    112    "           "       H     OCH.sub.3                                            CH.sub.3                                                    N    113    "           "       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    114    "           "       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    115    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    116    "           "       H     OCH.sub.3                                            CH.sub.3                                                    CH    117    "           "       H     OCH.sub.3                                            Cl      CH    118    "           "       H     CH.sub.3                                            CH.sub.3                                                    CH    119    "           "       H     OCH.sub.3                                            OCH.sub.3                                                    N    120    "           "       H     OCH.sub.3                                            CH.sub.3                                                    N    121    "           "       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    122    "           "       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    123    "           6-C.sub.2 H.sub.5                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    124    "           6-C.sub.4 H.sub.9                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    126    "           6-OC.sub.2 H.sub.5                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    127    "           6-OCH.sub.2 CF.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    128    "           6-SCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    129    "           6-SO.sub.2 CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    130    "           6-NO.sub.2                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    131    "           6-CO.sub.2 CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    132    "           6-Br    H     OCH.sub.3                                            OCH.sub.3                                                    CH    133    "           6-CF.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    134    "           6-OCF.sub.3                               R     OCH.sub.3                                            OCH.sub.3                                                    CH    135    "           6-OCF.sub.2 H                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    136    OSO.sub.2 N(CH.sub.3).sub.2                       H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    155-157    137    "           H       CH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    138    "           H       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    139    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    140    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    141    "           H       H     CH.sub.3                                            CH.sub.3                                                    N    142    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N     137-138 (dec.)    143    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N    144    "           H       H     OCH.sub.3                                            Cl      CH    145    "           H       H     OCF.sub.2 H                                            CH.sub.3                                                    CH    145    "           H       H     OCF.sub.2 H                                            OCF.sub.2 H                                                    CH    147    "           H       H     OCH.sub.3                                            Br      CH    148    "           H       H     OCH.sub.3                                            OC.sub.2 H.sub.5                                                    CH    149    "           H       H     OCH.sub.3                                            SCH.sub.3                                                    CH    150    "           H       H     OCH.sub.3                                            OC.sub.2 H.sub.5                                                    N    151    "           H       H     OCH.sub.3                                            OC.sub.2 H.sub.7                                                    CH    152    "           H       H     OCH.sub.3                                            Cl      N    153    "           H       H     Cl     OC.sub.2 H.sub.5                                                    CH    154    "           H       H     OC.sub.2 H.sub.5                                            OC.sub.2 H.sub.5                                                    CH    155    "           H       H     C.sub.2 H.sub.5                                            OCH.sub.3                                                    CH    156    "           H       H     CF.sub.3                                            OCH.sub.3                                                    CH    157    "           H       H     OCH.sub.2 CF.sub.3                                            CH.sub.3                                                    CH    158    "           H       H     OCH.sub.2 CF.sub.3                                            OCH.sub.3                                                    CH    159    "           H       H     OCH.sub.2 CF.sub.2                                            OCH.sub.2 CF.sub.3                                                    CH    160    "           H       H     OCH.sub.2 CF.sub.3                                            OCH.sub.3                                                    N    161    "           H       H     OCH.sub.3                                            CH(OCH.sub.2).sub.2                                                    CH    162    "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    163    "           "       H     OCH.sub.3                                            CH.sub.3                                                    CH    164    "           "       H     OCH.sub.3                                            Cl      CH    165    "           "       H     CH.sub.3                                            CH.sub.3                                                    CH    166    "           "       H     OCH.sub.3                                            OCH.sub.3                                                    N    167    "           "       H     OCH.sub.3                                            CH.sub.3                                                    N    168    "           "       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    169    "           "       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    170    "           5-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    171    "           "       H     OCH.sub.3                                            CH.sub.3                                                    CH    172    "           "       H     OCH.sub.3                                            Cl      CH    173    "           "       CH.sub.3                                     CH.sub.3                                            CH    174    "           "       H     OCH.sub.3                                            OCH.sub.3                                                    N    175    "           "       H     OCH.sub.3                                            CH.sub.3                                                    N    176    "           "       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    177    "           "       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    178    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    179    "           "       H     OCH.sub.3                                            CH.sub.3                                                    CH    180    "           "       H     OCH.sub.3                                            Cl      CH    181    "           "       H     CH.sub.3                                            CH.sub.3                                                    CH    182    "           "       H     OCH.sub.3                                            OCH.sub.3                                                    N    183    "           "       H     OCH.sub.3                                            CH.sub.3                                                    N    184    "           "       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    185    "           "       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    186    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    187    "           "       H     OCH.sub.3                                            CH.sub.3                                                    CH    188    "           "       H     OCH.sub.3                                            Cl      CH    189    "           "       H     CH.sub.3                                            CH.sub.3                                                    CH    190    "           "       H     OCH.sub.3                                            OCH.sub.3                                                    N    191    "           "       H     OCH.sub.3                                            CH.sub.3                                                    N    192    "           "       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    193    "           "       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    194    "           5-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    195    "           "       H     OCH.sub.3                                            CH.sub.3                                                    CH    196    "           "       H     OCH.sub.3                                            Cl      CH    197    "           "       H     CH.sub.3                                            CH.sub.3                                                    CH    198    "           "       H     OCH.sub.3                                            OCH.sub.3                                                    N    199    "           "       H     OCH.sub.3                                            CH.sub.3                                                    N    200    "           "       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    201    "           "       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    202    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    203    "           "       H     OCH.sub.3                                            CH.sub.3                                                    CH    204    "           "       H     OCH.sub.3                                            Cl      CH    205    "           "       H     CH.sub.3                                            CH.sub.3                                                    CH    206    "           "       H     OCH.sub.3                                            OCH.sub.3                                                    N    207    "           "       H     OCH.sub.3                                            CH.sub.3                                                    N    208    "           "       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    209    "           "       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    210    "           4-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    211    "           "       H     OCH.sub.3                                            CH.sub.3                                                    CH    212    "           "       H     OCH.sub.3                                            Cl      CH    213    "           "       H     CH.sub.3                                            CH.sub.3                                                    CH    214    "           "       H     OCH.sub.3                                            OCH.sub.3                                                    N    215    "           "       H     OCH.sub.3                                            CH.sub.3                                                    N    216    "           "       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    217    "           "       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    218    "           5-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    219    "           "       H     OCH.sub.3                                            CH.sub.3                                                    CH    220    "           "       H     OCH.sub.3                                            Cl      CH    221    "           "       H     CH.sub.3                                            CH.sub.3                                                    CH    222    "           "       H     OCH.sub.3                                            OCH.sub.3                                                    N    223    "           "       H     OCH.sub.3                                            CH.sub.3                                                    N    224    "           "       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    225    "           "       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    226    "           6-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    227    "           "       H     OCH.sub.3                                            CH.sub.3                                                    CH    228    "           "       H     OCH.sub.3                                            Cl      CH    229    "           "       H     CH.sub.3                                            CH.sub.3                                                    CH    230    "           "       H     OCH.sub.3                                            OCH.sub.3                                                    N    231    "           "       H     OCH.sub.3                                            CH.sub.3                                                    N    232    "           "       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    233    "           "       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    234    "           4-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    235    "           "       H     OCH.sub.3                                            CH.sub.3                                                    CH    236    "           "       H     OCH.sub.3                                            Cl      CH    237    "           "       H     CH.sub.3                                            CH.sub.3                                                    CH    238    "           "       H     OCH.sub.3                                            OCH.sub.3                                                    N    239    "           "       H     OCH.sub.3                                            CH.sub.3                                                    N    240    "           "       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    241    "           "       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    242    "           5-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    243    "           "       H     OCH.sub.3                                            CH.sub.3                                                    CH    244    "           "       H     OCH.sub.3                                            Cl      CH    245    "           "       H     CH.sub.3                                            CH.sub.3                                                    CH    246    "           "       H     OCH.sub.3                                            OCH.sub.3                                                    N    247    "           "       H     OCH.sub.3                                            CH.sub.3                                                    N    248    "           "       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    249    "           "       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    250    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    251    "           "       H     OCH.sub.3                                            CH.sub.3                                                    CH    252    "           "       H     OCH.sub.3                                            Cl      CH    253    "           "       H     CH.sub.3                                            CH.sub.3                                                    CH    254    "           "       H     OCH.sub.3                                            OCH.sub.3                                                    N    255    "           "       H     OCH.sub.3                                            CH.sub.3                                                    N    256    "           "       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    257    "           "       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    258    "           6-C.sub.2 H.sub.5                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    259    "           6-C.sub.4 H.sub.9                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    260    "           6-OC.sub.2 H.sub.5                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    261    "           6-OCH.sub.2 CF.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    262    "           6-SCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    263    "           6-SO.sub.2 CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    264    "           6-NO.sub.2                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    265    "           6-CO.sub.2 CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    266    "           6-Br    H     OCH.sub.3                                            OCH.sub.3                                                    CH    267    "           6-CF.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    268    "           6-OCF.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    269    "           6-OCF.sub.2 H                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    270            ##STR12##  H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    271    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    272    "           H       H     OCH.sub.3                                            Cl      CH    273    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    274    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N    275    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N    276    "           H       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    277    "           H       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    278    "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    279    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    280    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    281    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    282    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    283    OSO.sub.2 N(CH.sub.3)OCH.sub.3                       H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    284            ##STR13##  H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    285    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    286    "           H       H     OCH.sub.3                                            Cl      CH    287    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    288    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N    289    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N    290    "           H       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    291    "           H       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    292    "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    293    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    294    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    295    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    296    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    297    OSO.sub.2 N(Allyl).sub.2                       H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    298            ##STR14##  H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    157-158    299    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    151-153 (D.)    300    "           H       H     OCH.sub.3                                            Cl      CH    301    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    159-160 (D.)    302    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N    303    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N     146-149 (D.)    304    "           H       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    305    "           H       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    306    "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    307    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    308    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    309    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    310    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    311    "           6-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    312            ##STR15##  H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    158-159    313    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    170-171    314    "           H       H     OCH.sub.3                                            Cl      CH    315    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    169-170    316    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N    317    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N     155    318    "           H       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    319    "           H       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    320    "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    321    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    322    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    323    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    324    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    325    "           6-F     R     OCH.sub.3                                            OCH.sub.3                                                    CH    326            ##STR16##  H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    173-174 (D.)    327    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    328    "           H       H     OCH.sub.3                                            Cl      CH    329    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    185-186 (D.)    330    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N    331    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N    332    "           H       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    333    "           H       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    334    "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    335    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    336    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    337    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    338    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    339    "           6-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    340            ##STR17##  H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    141-142 (D.)    341    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    342    "           H       H     OCH.sub.3                                            Cl      CH    343    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    344    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N    345    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N    346    "           H       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    347    "           H       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    348    4-CH.sub.3  H       OCH.sub.3                                     OCH.sub.3                                            CH    349    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    350    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    351    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    352    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    353    "           6-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    354    NHSO.sub.2 CH.sub.3                       H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    191-192 (D.)    355    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    356    "           H       H     OCH.sub.3                                            Cl      CH    357    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    358    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N    359    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N    360    "           H       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    361    "           H       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    362    "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    363    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    364    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    365    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    366    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    367    "           6-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    368    NHSO.sub.2 C.sub.2 H.sub.5                       H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    369    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    370    "           H       H     OCH.sub.3                                            Cl      CH    371    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    372    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N    373    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N    374    "           H       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    375    "           H       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    376    "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    377    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    378    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    379    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    380    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    381    "           6-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    382    NHSO.sub.2 C.sub.3 H.sub.7                       H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    383    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    384    "           H       H     OCH.sub.3                                            Cl      CH    385    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    386    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N    387    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N    388    "           H       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    389    "           H       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    390    "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    391    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    392    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    393    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    394    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    395    "           6-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    396    NHSO.sub.2 C.sub.8 H.sub.5                       H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    397    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    398    "           H       H     OCH.sub.3                                            Cl      CH    399    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    401    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N    402    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N    403    "           H       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    404    "           H       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    405    "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    406    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    407    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    408    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    409    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    410    "           6-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    411    N(SO.sub.2 CH.sub.3).sub.2                       H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    219-220 (D.)    412    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    413    "           H       H     OCH.sub.3                                            Cl      CH    414    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    415    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N    416    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N    417    "           H       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    418    "           H       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    419    "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    420    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    421    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    422    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    423    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    424    "           6-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    425    N(SO.sub.2 C.sub.2 H.sub.5).sub.2                       H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    426    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    427    "           H       H     OCH.sub.3                                            Cl      CH    428    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    429    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N    430    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N    431    "           H       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    432    "           H       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    433    "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    434    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    435    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    436    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    437    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    438    "           6-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    439    N(CH.sub.3)SO.sub.2 CH.sub.3                       H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    177-178    440    "           H       CH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    152-153    441    "           H       CH.sub.3                                     OCH.sub.3                                            CH.sub.3                                                    N    442    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    185-186 (D.)    443    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    169-170 (D.)    444    "           H       H     CH.sub.3                                            OC.sub.2 H.sub.5                                                    CH    445    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N     158-159 (D.)    446    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N     173-174 (D.)    447    "           H       H     OCH.sub.3                                            Cl      CH    167-169    448    "           H       H     OCF.sub.2 H                                            CH.sub.3                                                    CH    449    "           H       H     OCF.sub.2 H                                            OCF.sub.2 H                                                    CH    450    "           H       H     OCH.sub.3                                            Br      CH    451    "           H       H     OCH.sub.3                                            OC.sub.2 H.sub.5                                                    CH    452    "           H       H     OCH.sub.3                                            SCH.sub.3                                                    CH    453    "           H       H     OCH.sub.3                                            OC.sub.2 H.sub.5                                                    N    454    "           H       H     OCH.sub.3                                            OC.sub.3 H.sub.7                                                    CH    455    "           H       H     CH.sub.3                                            Cl      CH    168-169 (D.)    456    "           H       H     Cl     OC.sub.2 H.sub.5                                                    CH    457    "           H       H     OC.sub.2 H.sub.5                                            OC.sub.2 H.sub.5                                                    CH    458    "           H       H     C.sub.2 H.sub.5                                            OCH.sub.3                                                    CH    459    "           H       H     CF.sub.3                                            OCH.sub.3                                                    CH    460    "           H       H     OCH.sub.2 CF.sub.3                                            CH.sub.3                                                    CH    461    "           H       H     OCH.sub.2 CF.sub.3                                            OCH.sub.3                                                    CH    462    "           H       H     OC.sub.2 CF.sub.3                                            OC.sub.2 CF.sub.3                                                    CH    463    "           H       H     OC.sub.2 CF.sub.3                                            OCH.sub.3                                                    N    464    "           H       H     OCH.sub.3                                            CH(OCH.sub.3).sub.2                                                    CH    465    "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    466    "           "       H     OCH.sub.3                                            CH.sub.3                                                    CH    467    "           "       H     OCH.sub.3                                            Cl      CH    468    "           "       H     CH.sub.3                                            CH.sub.3                                                    CH    469    "           "       H     OCH.sub.3                                            OCH.sub.3                                                    N    470    "           "       H     OCH.sub.3                                            CH.sub.3                                                    N    471    "           "       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    472    "           "       CH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    473    "           5-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    474    "           "       H     OCH.sub.3                                            CH.sub.3                                                    CH    475    "           "       H     OCH.sub.3                                            Cl      CH    476    "           "       H     CH.sub.3                                            CH.sub.3                                                    CH    477    "           "       H     OCH.sub.3                                            OCH.sub.3                                                    N    478    "           "       H     OCH.sub.3                                            CH.sub.3                                                    N    479    "           "       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    480    "           "       CH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    481    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    185    482    "           "       H     OCH.sub.3                                            CH.sub.3                                                    CH    483    "           "       H     OCH.sub.3                                            Cl      CH    484    "           "       H     CH.sub.3                                            CH.sub.3                                                    CH    485    "           "       H     OCH.sub.3                                            OCH.sub.3                                                    N    486    "           "       H     OCH.sub.3                                            CH.sub.3                                                    N    487    "           "       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    488    "           "       CH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    489    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    490    "           "       H     OCH.sub.3                                            CH.sub.3                                                    CH    491    "           "       H     OCH.sub.3                                            Cl      CH    492    "           "       H     CH.sub.3                                            CH.sub.3                                                    CH    493    "           "       H     OCH.sub.3                                            OCH.sub.3                                                    N    494    "           "       H     OCH.sub.3                                            CH.sub.3                                                    N    495    "           "       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    496    "           "       CH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    497    "           5-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    498    "           "       H     OCH.sub.3                                            CH.sub.3                                                    CH    499    "           "       H     OCH.sub.3                                            Cl      CH    500    "           "       H     CH.sub.3                                            CH.sub.3                                                    CH    501    "           "       H     OCH.sub.3                                            OCH.sub.3                                                    N    502    "           "       H     OCH.sub.3                                            CH.sub.3                                                    N    503    "           "       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    504    "           "       CH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    505    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    506    "           "       H     OCH.sub.3                                            CH.sub.3                                                    CH    507    "           "       H     OCH.sub.3                                            Cl      CH    508    "           "       H     CH.sub.3                                            CH.sub.3                                                    CH    509    "           "       H     OCH.sub.3                                            OCH.sub.3                                                    N    510    "           "       H     OCH.sub.3                                            CH.sub.3                                                    N    511    "           "       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    512    "           "       CH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    513    "           4-CF.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    514    "           "       H     OCH.sub.3                                            CH.sub.3                                                    CH    515    "           "       H     OCH.sub.3                                            Cl      CH    516    "           "       H     CH.sub.3                                            CH.sub.3                                                    CH    517    "           "       H     OCH.sub.3                                            OCH.sub.3                                                    N    518    "           "       H     OCH.sub.3                                            CH.sub.3                                                    N    519    "           4-F     H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    520    "           "       CH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    521    "           5-CF.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    522    "           "       H     OCH.sub.3                                            CH.sub.3                                                    CH    523    "           "       H     OCH.sub.3                                            Cl      CH    524    "           "       H     CH.sub.3                                            CH.sub.3                                                    CH    525    "           "       H     OCH.sub.3                                            OCH.sub.3                                                    N    526    "           "       H     OCH.sub.3                                            CH.sub.3                                                    N    527    "           5-F     H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    528    "           "       CH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    529    "           6-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    530    "           "       H     OCH.sub.3                                            CH.sub.3                                                    CH    531    "           "       H     OCH.sub.3                                            Cl      CH    532    "           "       H     CH.sub.3                                            CH.sub.3                                                    CH    533    "           "       H     OCH.sub.3                                            OCH.sub.3                                                    N    534    "           "       H     OCH.sub.3                                            CH.sub.3                                                    N    535    "           "       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    536    "           "       CH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    537    "           4-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    538    "           "       H     OCH.sub.3                                            CH.sub.3                                                    CH    539    "           "       H     OCH.sub.3                                            Cl      CH    540    "           "       H     CH.sub.3                                            CH.sub.3                                                    CH    541    "           "       OCH.sub.3                                     OCH.sub.3                                            N    542    "           "       H     OCH.sub.3                                            CH.sub.3                                                    N    543    "           "       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    544    "           "       CH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    545    "           5-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    546    "           "       H     OCH.sub.3                                            CH.sub.3                                                    CH    547    "           "       H     OCH.sub.3                                            Cl      CH    548    "           "       H     CH.sub.3                                            CH.sub.3                                                    CH    549    "           "       H     OCH.sub.3                                            OCH.sub.3                                                    N    550    "           "       H     OCH.sub.3                                            CH.sub.3                                                    N    551    "           "       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    552    "           "       CH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    553    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    554    "           "       H     OCH.sub.3                                            CH.sub.3                                                    CH    555    "           "       H     OCH.sub.3                                            Cl      CH    556    "           "       H     CH.sub.3                                            CH.sub.3                                                    CH    557    "           "       H     OCH.sub.3                                            OCH.sub.3                                                    N    558    "           "       H     OCH.sub.3                                            CH.sub.3                                                    N    559    "           "       H     OCH.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    560    "           "       CH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    561    "           6-C.sub.2 H.sub.5                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    562    "           6-C.sub.4 H.sub.9                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    563    "           6-OC.sub.2 H.sub.5                               R     OCH.sub.3                                            OCH.sub.3                                                    CH    564    "           6-OC.sub.2 CF.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    565    "           6-SCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    566    "           6-SO.sub.2 CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    567    "           6-NO.sub.2                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    568    "           6-CO.sub.2 CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    569    "           6-Br    H     OCH.sub.3                                            OCH.sub.3                                                    CH    570    "           6-CF.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    571    "           6-OCF.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    572    "           6-OCF.sub.2 H                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    573    N(Et)SO.sub.2 CH.sub.3                       H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    188 (D.)    574    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    575    "           H       H     OCH.sub.3                                            Cl      CH    576    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    577    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N    578    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N    579    "           H       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    580    "           H       CH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    581    "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    582    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    583    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    584    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    585    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    586    "           6-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    587    N(Pr)SO.sub.2 CH.sub.3                       H       H     OCH.sub.3                                            CH      182-183 (D.)    588    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    589    "           H       H     OCH.sub.3                                            Cl      CH    590    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    591    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N    592    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N    593    "           H       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    594    "           H       CH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    595    "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    596    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    597    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    598    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    599    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    600    "           6-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    601    N(i-Pr)SO.sub.2 CH.sub.3                       H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    195 (D.)    602    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    603    "           H       H     OCH.sub.3                                            Cl      CH    604    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    605    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N    606    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N    607    "           H       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    608    "           H       CH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    609    "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    610    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    611    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    612    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    613    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    614    "           6-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    615    N(i-Bu)SO.sub.2 CH.sub.3                       H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    166-167    616    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    617    "           H       H     OCH.sub.3                                            Cl      CH    618    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    619    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N    620    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N    621    "           H       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    622    "           H       CH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    623    "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    624    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    625    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    626    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    627    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    628    "           6-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    629    N(CF.sub.3)SO.sub.2 CH.sub.3                       H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    630    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    631    "           H       H     OCH.sub.3                                            Cl      CH    632    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    633    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N    634    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N    635    "           H       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    636    "           H       HCH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    637    "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    638    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    639    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    640    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    641    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    642    "           6-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    643    N(CHF.sub.2)SO.sub.2 CH.sub.3                       H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    644    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    645    "           H       H     OCH.sub.3                                            Cl      CH    646    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    647    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N    648    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N    649    "           H       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    650    "           H       CH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    651    "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    652    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    653    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    654    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    655    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    656    "           6-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    657            ##STR18##  H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    658    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    659    "           H       H     OCH.sub.3                                            Cl      CH    660    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    661    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N    662    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N    663    "           H       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    664    "           H       CH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    665    "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    666    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    667    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    668    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    669    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    670    "           6-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    671            ##STR19##  H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    672    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    673    "           H       H     OCH.sub.3                                            Cl      CH    674    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    675    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N    676    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N    677    "           H       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    678    "           H       CH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    679    "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    680    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    681    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    682    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    683    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    684    "           6-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    685            ##STR20##  H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    686    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    687    "           H       H     OCH.sub.3                                            Cl      CH    688    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    689    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N    690    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N    691    "           H       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    692    "           H       CH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    693    "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    694    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    695    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    696    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    697    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    698    "           6-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    699            ##STR21##  H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    700    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    701    "           H       H     OCH.sub.3                                            Cl      CH    702    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    703    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N    704    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N    706    "           H       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    707    "           H       CH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    708    "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    709    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    710    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    711    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    712    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    713    "           6-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    714            ##STR22##  H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    715    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    716    "           H       H     OCH.sub.3                                            Cl      CH    717    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    718    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N    719    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N    720    "           H       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    721    "           H       CH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    722    "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    723    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    724    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    725    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    726    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    727    "           6-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    728            ##STR23##  H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    729    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    730    "           H       H     OCH.sub.3                                            Cl      CH    731    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    732    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N    733    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N    734    "           H       H     OC.sub.2 H.sub.5                                            NNCH.sub.3                                                    N    735    "           H       CH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    735    "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    737    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    738    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    739    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    740    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    741    "           6-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    742            ##STR24##  H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    743    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    744    "           H       H     OCH.sub.3                                            Cl      CH    745    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    746    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N    747    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N    748    "           H       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    749    "           H       CH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    750    "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    751    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    752    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    753    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    754    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    755    "           6-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    756            ##STR25##  H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    208-210 (D.)    757    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    758    "           H       H     OCH.sub.3                                            Cl      CH    759    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    760    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N    761    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N    762    "           H       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    736    "           H       CH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    764    "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    765    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    766    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    767    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    768    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    769    "           6-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    770            ##STR26##  H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    167-168 (D.)    771    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    772    "           H       H     OCH.sub.3                                            Cl      CH    773    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    774    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N    775    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N    776    "           H       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    777    "           H       CH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    778    "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    779    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    780    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    781    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    782    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    783    "           6-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    784            ##STR27##  H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    785    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    786    "           H       H     OCH.sub.3                                            Cl      CH    787    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    788    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N    789    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N    790    "           H       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    791    "           H       CH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    792    "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    793    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    794    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    795    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    796    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    797    "           6-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    798            ##STR28##  H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    195 (D.)    799    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    800    "           H       H     OCH.sub.3                                            Cl      CH    801    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    802    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N    803    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N    804    "           H       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    805    "           H       CH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    806    "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    807    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    808    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    809    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    810    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    811    "           6-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    812            ##STR29##  H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    192-193 (D.)    813    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    814    "           H       H     OCH.sub.3                                            Cl      CH    815    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    816    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N    817    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N    818    "           H       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    819    "           H       CH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    820    "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    821    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    822    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    823    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    824    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    825    "           6-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    826    N(OCH.sub.3)SO.sub.2 CH.sub.3                       H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    827    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    828    "           H       H     OCH.sub.3                                            Cl      CH    829    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    830    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N    831    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N    832    "           H       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    833    "           H       CH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    834    "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    835    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    836    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    837    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    838    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    839    "           6-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    840    N(CH.sub.3)SO.sub.2 CF.sub.3                       H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    841    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    842    "           H       H     OCH.sub.3                                            Cl      CH    843    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    844    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N    845    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N    846    "           H       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    847    "           CH.sub.3                               OCH.sub.3                                     OCH.sub.3                                            CH    848    "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    849    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    850    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    851    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    852    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    853    "           6-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    854    N(CH.sub.3)SO.sub.2 Et                       H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    176-177    855    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    856    "           H       H     OCH.sub.3                                            Cl      CH    857    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    858    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N    859    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N    860    "           H       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    861    "           H       CH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    862    "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    863    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    864    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    193-194 (D.)    865    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    866    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    867    "           6-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    868    N(CH.sub.3)SO.sub.2 Ph                       H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    869    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    870    "           H       H     OCH.sub.3                                            Cl      CH    871    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    872    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N    873    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N    874    "           H       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    875    "           H       CH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    876    "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    877    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    878    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    879    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    880    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    881    "           6-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    882    N(CH.sub.3)SO.sub.2 NMe.sub.2                       H       H     OCH.sub.3                                            OCH.sub.3                                                    CH    883    "           H       H     OCH.sub.3                                            CH.sub.3                                                    CH    884    "           H       H     OCH.sub.3                                            Cl      CH    885    "           H       H     CH.sub.3                                            CH.sub.3                                                    CH    886    "           H       H     OCH.sub.3                                            OCH.sub.3                                                    N    887    "           H       H     OCH.sub.3                                            CH.sub.3                                                    N    888    "           H       H     OC.sub.2 H.sub.5                                            NHCH.sub.3                                                    N    889    "           H       CH.sub.3                                     OCH.sub.3                                            OCH.sub.3                                                    CH    890    "           4-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    891    "           4-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    892    "           6-CH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    893    "           6-OCH.sub.3                               H     OCH.sub.3                                            OCH.sub.3                                                    CH    894    "           6-Cl    H     OCH.sub.3                                            OCH.sub.3                                                    CH    895    "           6-F     H     OCH.sub.3                                            OCH.sub.3                                                    CH    __________________________________________________________________________

                                      TABLE 2    __________________________________________________________________________     ##STR30##    Cpd. No.         R.sup.1   R.sup.2                        R.sup.3                           X   Y    Z  M.p. [°C.]    __________________________________________________________________________    896  I         H    H  OCH.sub.3                               OCH.sub.3                                    CH    897  "         H    H  OCH.sub.3                               CH.sub.3                                    CH    898  "         H    H  OCH.sub.3                               Cl   CH    899  "         H    H  CH.sub.3                               CH.sub.3                                    CH    900  "         H    H  OCH.sub.3                               OCH.sub.3                                    N    901  "         H    H  OCH.sub.3                               CH.sub.3                                    N    902  "         H    H  OC.sub.2 H.sub.5                               NHCH.sub.3                                    N    903  "         H    CH.sub.3                           OCH.sub.3                               OCH.sub.3                                    CH    904  "         4-CH.sub.3                        H  OCH.sub.3                               OCH.sub.3                                    CH    905  "         6-CH.sub.3                        H  OCH.sub.3                               OCH.sub.3                                    CH    906  "         4-Cl H  OCH.sub.3                               OCH.sub.3                                    CH    907  "         6-Cl H  OCH.sub.3                               OCH.sub.3                                    CH    908  "         4-F  H  OCH.sub.3                               OCH.sub.3                                    CH    909  "         6-F  H  OCH.sub.3                               OCH.sub.3                                    CH    910  "         4-OCH.sub.3                        H  OCH.sub.3                               OCH.sub.3                                    CH    911  "         6-OCH.sub.3                        H  OCH.sub.3                               OCH.sub.3                                    CH    912  OSO.sub.2 N(CH.sub.3).sub.2                   H    H  OCH.sub.3                               OCH.sub.3                                    CH    913  "         4-CH.sub.3                        H  OCH.sub.3                               OCH.sub.3                                    CH    914  "         6-CH.sub.3                        H  OCH.sub.3                               OCH.sub.3                                    CH    915  "         4-Cl H  OCH.sub.3                               OCH.sub.3                                    CH    916  "         6-Cl H  OCH.sub.3                               OCH.sub.3                                    CH    917  "         4-F  H  OCH.sub.3                               OCH.sub.3                                    CH    918  "         6-F  H  OCH.sub.3                               OCH.sub.3                                    CH    919  "         4-OCH.sub.3                        H  OCH.sub.3                               OCH.sub.3                                    CH    920  "         6-OCH.sub.3                        H  OCH.sub.3                               OCH.sub.3                                    CH    921  N(CH.sub.3)SO.sub.2 CH.sub.3                   H    H  OCH.sub.3                               OCH.sub.3                                    CH    922  "         H    H  OCH.sub.3                               CH.sub.3                                    CH    923  "         H    H  OCH.sub.3                               Cl   CH    924  "         H    H  CH.sub.3                               CH.sub.3                                    CH    925  "         H    H  OCH.sub.3                               OCH.sub.3                                    N    926  "         H    H  OCH.sub.3                               CH.sub.3                                    N    927  "         H    H  OC.sub.2 H.sub.5                               NHCH.sub.3                                    N    928  "         H    CH.sub.3                           OCH.sub.3                               OCH.sub.3                                    CH    929  "         4-CH.sub.3                        H  OCH.sub.3                               OCH.sub.3                                    CH    930  "         6-CH.sub.3                        H  OCH.sub.3                               OCH.sub.3                                    CH    931  "         4-Cl H  OCH.sub.3                               OCH.sub.3                                    CH    932  "         6-Cl H  OCH.sub.3                               OCH.sub.3                                    CH    933  "         4-F  H  OCH.sub.3                               OCH.sub.3                                    CH    934  "         6-F  H  OCH.sub.3                               OCH.sub.3                                    CH    935  "         4-OCH.sub.3                        H  OCH.sub.3                               OCH.sub.3                                    CH    936  "         6-OCH.sub.3                        H  OCH.sub.3                               OCH.sub.3                                    CH    937  NHSO.sub.2 CH.sub.3                   H    H  OCH.sub.3                               OCH.sub.3                                    CH    938  NHSO.sub.2 C.sub.2 H.sub.5                   H    H  OCH.sub.3                               OCH.sub.3                                    CH    939  N(SO.sub.2 CH.sub.3).sub.2                   H    H  OCH.sub.3                               OCH.sub.3                                    CH    940  N(CH.sub.3)SO.sub.2 Et                   H    H  OCH.sub.3                               OCH.sub.3                                    CH    941  N(Et)SO.sub.2 CH.sub.3                   H    H  OCH.sub.3                               OCH.sub.3                                    CH    __________________________________________________________________________

                  TABLE 3    ______________________________________     ##STR31##    Cpa. No.            R.sup.1        A    ______________________________________    942     I                            ##STR32##    943     OSO.sub.2 N(CH.sub.3).sub.2                            ##STR33##    944     I                            ##STR34##    945     OSO.sub.2 N(CH.sub.3).sub.3                            ##STR35##    946     I                            ##STR36##    947     OSO.sub.2 N(CH.sub.3).sub.2                            ##STR37##    948     I                            ##STR38##    949     OSO.sub.2 N(CH.sub.3).sub.2                            ##STR39##    950     I                            ##STR40##    951     OSO.sub.2 N(CH.sub.3).sub.2                            ##STR41##    952     I                            ##STR42##    953     OSO.sub.2 N(CH.sub.3).sub.2                            ##STR43##    954     I                            ##STR44##    955     N(CH.sub.3)SO.sub.2 CH.sub.3                            ##STR45##    956     "                            ##STR46##    957     "                            ##STR47##    958     "                            ##STR48##    959     "                            ##STR49##    960     N(CH.sub.3)SO.sub.2 CH.sub.3                            ##STR50##    961     "                            ##STR51##    962     "                            ##STR52##    963     "                            ##STR53##    964     "                            ##STR54##    965     "                            ##STR55##    966     "                            ##STR56##    967     "                            ##STR57##    ______________________________________

                  TABLE 4    ______________________________________     ##STR58##    Cpd. No.           R.sup.1        R.sup.2    M.p. [°C.]    ______________________________________    968    I              H          247-250 (dec.)    969    "              4-CH.sub.3    970    "              5-CH.sub.3    971    "              6-CH.sub.3    972    "              4-OCH.sub.3    973    "              5-OCH.sub.3    974    "              6-OCH.sub.3    975    "              4-Cl    976    "              5-Cl    977    "              6-Cl    978    "              4-F    979    "              5-F    980    "              6-F    981    "              6-C.sub.2 H.sub.5    982    "              6-C.sub.4 H.sub.9    983    "              6-OC.sub.2 H.sub.5    984    "              6-OCH.sub.2 CF.sub.3    985    "              6-SCH.sub.3    986    "              6-SO.sub.2 CH.sub.3    987    "              6-NO.sub.2    988    "              6-CO.sub.2 CH.sub.3    989    "              6-Br    990    "              6-CF.sub.3    991    "              6-OCF.sub.3    992    "              6-OCF.sub.2 H    993    OSO.sub.2 N(CH.sub.3).sub.2                          H          oil    994    "              4-CH.sub.3    995    "              5-CH.sub.3    996    "              6-CH.sub.3    997    "              4-OCH.sub.3    998    "              5-OCH.sub.3    999    "              6-OCH.sub.3    1000   "              4-Cl    1001   "              5-Cl    1002   "              6-Cl    1002   "              4-F    1004   "              5-F    1005   "              6-F    1006   "              6-C.sub.2 H.sub.5    1007   "              6-C.sub.4 H.sub.9    1008   "              6-OC.sub.2 H.sub.5    1009   "              6-OCH.sub.2 CF.sub.3    1010   "              6-SCH.sub.3    1011   "              6-SO.sub.2 CH.sub.3    1012   "              6-NO.sub.2    1013   "              6-CO.sub.2 CH.sub.3    1014   "              6-Br    1015   "              6-CF.sub.3    1016   "              6-OCF.sub.3    1017   "              6-OCF.sub.2 H    1018            ##STR59##     H    1019            ##STR60##     H    1020            ##STR61##     H          94-97    1021            ##STR62##     H          142-143    1022            ##STR63##     H          166-167    1023            ##STR64##     H          oil    1024   NHSO.sub.2 CH.sub.3                          H          176-178    1025   NHSO.sub.2 C.sub.2 H.sub.5                          H    1026   NHSO.sub.2 C.sub.3 H.sub.7                          H    1027   NHSO.sub.2 C.sub.6 H.sub.5                          H    1028   N(SO.sub.2 CH.sub.3).sub.2                          H          208    1029   N(SO.sub.2 C.sub.2 H.sub.5).sub.2                          H    1030   N(CH.sub.3)SO.sub.2 CH.sub.3                          H          175    1031   "              4-CH.sub.3    1032   "              5-CH.sub.3    1033   "              6-CH.sub.3 124    1034   "              4-OCH.sub.3    1035   "              5-OCH.sub.3    1036   "              6-OCH.sub.3    1037   "              4-Cl    1038   "              5-Cl    1039   "              6-Cl    1040   "              4-F    1041   "              5-F    1042   "              6-F    1043   "              6-C.sub.2 H.sub.5    1044   "              6-C.sub.4 H.sub.9    1045   "              6-OC.sub.2 H.sub.5    1046   "              6-OCH.sub.2 CF.sub.3    1047   "              6-SCH.sub.3    1048   "              6-SO.sub.2 CH.sub.3    1049   "              6-NO.sub.2    1050   "              6-CO.sub.2 CH.sub.3    1051   "              6-Br    1052   "              6-CF.sub.3    1053   "              6-OCF.sub.3    1054   "              6-OCF.sub.2 H    1055   N(Et)SO.sub.2 CH.sub.3                          H          178-179 (D.)    1056   N(Pr)SO.sub.2 CH.sub.3                          H          149-150    1057   N(i-Pr)SO.sub.2 CH.sub.3                          H          201    1058   N(i-Bu)SO.sub.2 CH.sub.3                          H          amorphous    1059            ##STR65##     H    1060            ##STR66##     H    1061            ##STR67##     H    1062            ##STR68##     H    1063            ##STR69##     H    1064            ##STR70##     H    1065            ##STR71##     H    1066            ##STR72##     H          143-144    1067            ##STR73##     H          138-141    1068            ##STR74##     H    1069            ##STR75##     H          200 (D.)    1070            ##STR76##     H          220-221 (D.)    1071   N(OCH.sub.3)SO.sub.2 CH.sub.3                          H    1072   N(CH.sub.3)SO.sub.2 C.sub.2 H.sub.5                          H          136-137    1073   N(CH.sub.3)SO.sub.2 CF.sub.3                          H    1074   N(CH.sub.3)SO.sub.2 Ph                          H          200-203    1075   N(CH.sub.3)SO.sub.2 N(Me).sub.2                          H    ______________________________________

B. FORMULATION EXAMPLES

a) A dusting agent is obtained by mixing 10 parts by weight of acompound of the formula (I) and 90 parts by weight of talc or inertmaterial and comminuting in a hammer mill.

b) A wettable powder which is easily dispersible in water is obtained bymixing 25 parts by weight of a compound of the formula (I), 64 parts byweight of kaolin-containingquartz as inert material, 10 parts by weightof potassium ligninsulfonate and 1 part by weight of sodiumoleoylmethyltaurate as wetting agent and dispersant and grinding in apin-disk mill.

c) A dispersion concentrate which is easily dispersible in water isobtained by mixing 20 parts by weight of a compound of the formula (I)with 6 parts by weight of alkylphenol polyglycol ether (®Triton X 207),3 parts by weight of isotridecanol polyglycol ether (8) EO) and 71 partsby weight of paraffinic mineral oil (boiling range, for example, about255° to over 277° C.) and grinding to a fineness of less than 5 micronsin a friction ball mill.

d) An emulsifiable concentrate is obtained from 15 parts by weight of acompound of the formula (I), 75 parts by weight of cyclohexane assolvent and 10 parts by weight of ethoxylated nonylphenol as emulsifier.

e) Granules which are dispersible in water are obtained by mixing

75 parts by weight of a compound of the formula (I),

10 parts by weight of calcium ligninsulfonate,

5 parts by weight of sodium lauryl sulfate,

3 parts by weight of polyvinyl alcohol and

7 parts by weight of kaolin,

grinding in a pinned-disk mill and granulating the powder in a fluidizedbed by spraying water as a granulating fluid.

f) Granules which are dispersible in water are also obtained byhomogenizing and precomminuting 25 parts by weight of a compound of theformula (I),

5 parts by weight of sodium 2,2'-dinaphthylmethane-6,6'-disulfonate,

2 parts by weight of sodium oleolymethyltaurate,

1 parts by weight of polyvinyl alcohol,

17 parts by weight of calcium carbonate and

50 parts by weight of water,

then grinding in a bead mill and atomizing the suspension thus obtainedin a spray tower by means of a single substance nozzle and drying.

g) Extruder granules are obtained by mixing 20 parts by weight of activecompound, 3 parts by weight of sodium ligninsulfonate, 1 part by weightof carboxymethylcellulose and 76 parts by weight of kaolin, grinding andmoistening with water. This mixture is extruded and then dried in astream of air.

C. Biological examples 1. Weed action pre-emergence

Seeds or pieces of rhizome of monocotyledon and dicotyledon weed plantswere planted in sandy loam soil in plastic pots and covered with earth.The compounds according to the invention formulated in the form ofwettable powders or emulsion concentrates were then applied in variousdosages to the surface of the covering earth as aqueous suspensions oremulsions using a water application rate of 600 to 800 1/ha afterconversion.

After the treatment, the pots were placed in a greenhouse and kept undergood growth conditions for the weeds. visual assessment of the plantsand the emergence damage was carried out in comparison to untreatedcontrols after the emergence of the experiment plants after anexperiment time of 3 to 4 weeks. As the assessment values show, thecompounds according to the invention have a good herbicidalpre-emergence activity against a broad spectrum of weed grasses andweeds (cf. Table 5).

                  TABLE 5    ______________________________________    Pre-emergence action of the compounds according    to the invention         Dose    Ex.  (kg     Herbicidal action    No.  a.i./ha)                 LOMU    ECCR  AVSA  STME  CHSE  SIAL    ______________________________________     1   0.3     5       5     5     5     5     5    136  0.3     5       5     4     5     5     5     4   0.3     5       5     5     5     5     5    411  0.3     5       5     5     5     5     5    354  0.3     5       5     5     5     5     5    439  0.3     5       5     5     5     5     5    312  0.3     4       4     2     4     4     5    326  0.3     2       2     2     3     3     4     7   0.3     5       5     5     5     5     5    299  0.3     5       5     4     5     5     5    443  0.3     5       5     5     5     5     5    301  0.3     2       2     2     2     2     3    298  0.3     5       5     4     5     5     5    313  0.3     3       3     2     4     3     5    446  0.3     5       3     5     4     3     5    445  0.3     5       4     5     5     2     4    756  0.3     5       5     5     5     5     5    442  0.3     5       5     5     5     5     5    455  0.3     3       2     2     3     3     5    770  0.3     5       5     5     5     5     5    854  0.3     5       5     5     5     5     5     8   0.3     5       5     5     5     5     5     5   0.3     5       5     5     5     5     5    142  0.3     5       5     5     5     5     5    340  0.3     5       5     3     5     5     5    573  0.3     5       5     5     5     5     5    ______________________________________     Abbreviations:     Ex. No. = Preparation example from TABLES 1 to 4     a.i. = active ingredient (based on pure active compound)     LOMU = Lolium multiflorum     ECCR = Echinochloa crusgalli     AVSA = Avena sativa     STME = Stellaria media     CHSE = Chrysanthemum segetum     STAL = Sinapis alba

2. Weed action post-emergence

Seeds or pieces of rhizome of monocotyledon and dicotyledon weeds wereplanted in sandy loam soil in plastic pots, covered with earth andraised in a greenhouse under good growth conditions. Three weeks aftersowing, the experimental plants were treated in the three-leaf stage.

The compounds according to the invention formulated as wettable powdersor as emulsion concentrates were sprayed onto the green parts of plantsin various dosages using a water application rate of 600 to 800 l/haafter conversion and, after a standing time of the experimental plantsin the greenhouse under optimum growth conditions of about 3 to 4 weeks,the action of the preparations was assessed visually in comparison tountreated controls.

The agents according to the invention also show a good herbicidalactivity post-emergence against a broad spectrum of economicallyimportant weed grasses and weeds (cf. Table 6).

                  TABLE 6    ______________________________________         Dose    Ex.  (kg     Herbicidal action    No.  a.i./ha)                 LOMU    ECCR  AVSA  STME  CHSE  SIAL    ______________________________________     1   0.3     5       5     5     5     5     5    136  0.3     3       4     1     5     5     5     4   0.3     5       5     5     5     5     5    411  0.3     5       5     4     5     5     5    354  0.3     5       5     5     5     5     5    439  0.3     5       5     5     5     5     5     7   0.3     5       5     5     5     5     5    299  0.3     3       3     2     3     2     5    443  0.3     5       5     5     5     3     5    298  0.3     3       5     2     4     3     5    445  0.3     3       2     2     3     4     3    756  0.3     5       4     3     4     4     5    442  0.3     5       2     3     3     2     4    770  0.3     5       3     3     3     3     3    854  0.3     4       5     4     4     5     5     8   0.3     5       5     5     5     3     5     5   0.3     5       5     5     5     5     5    142  0.3     4       2     2     4     1     3    340  0.3     3       3     0     5     2     5    573  0.3     5       5     5     5     5     5    ______________________________________     Abbreviations:     Ex. No. = Preparation example from TABLES 1 to 4     a.i. = active ingredient (based on pure active compound)     LOMU = Lolium multiflorum     ECCR = Echinochloa crusgalli     AVSA = Avena sativa     STME = Stellaria media     CHSE = Chrysanthemum segetum     STAL = Sinapis alba

3. Crop plant tolerability

In further experiments in a greenhouse, seeds of a relatively largenumber of crop plants and weeds were planted in sandy loam soil andcovered with earth.

Some of the pots were immediately treated as described under 1 and theothers were placed in a greenhouse until the plants had developed two tothree true leaves and then sprayed with the substances according to theinvention in various dosages, as described under 2.

Four to five weeks after application and standing in a greenhouse, itwas determined by means of optical assessment that the compoundsaccording to the invention left dicotyl crops such as, for example,soya, cotton, rape, sugarbeet and potatoes undamaged pre- andpost-emergence even at high active compound dosages. Moreover, somesubstances also spared gramineous crops such as, for example, barley,wheat, rye, sorghum millet, corn and rice. The compounds of the formula(I) thus have a high selectivity when used for controlling undesiredplant growth in agricultural crops.

We claim:
 1. A compound of the formula (I) or its salts ##STR77## inwhich R¹ is iodine,R² is H, (C₁ -C₄)alkyl, (C₁ -C₃)haloalkyl, halogen,NO₂, CN, (C₁ -C₃)alkoxy, (C₁ -C₃)haloalkoxy, (C₁ -C₃)alkylthio, (C₁ -C₃)alkoxy-(C₁ -C₃)alkyl, (C₁ -C₃)alkoxycarbonyl, (C₁ -C₃)alkylamino, di[(C₁-C₃)alkyl]amino, (C₁ -C₃)alkylsulfinyl, (C₁ -C₃)alkylsulfonyl, SO₂NR^(a) R^(b) or C(O)NR^(a) R^(b), R^(a) and R^(b))independently of oneanother are H, (C₁ -C₃)alkyl, (C₃ -C₄)alkenyl, propargyl, or togetherare --(CH₂)₄ --, --(CH₂)₅ -- or CH₂ CH₂ OCH₂ CH₂ --, R³ is H or CH₃, nis zero or 1, W is O or S, A is a radical of the formula ##STR78## X isH, halogen, (C₁ -C₃)alkyl, (C₁ -C₃)alkoxy, where the two last-mentionedradicals are unsubstituted or monosubstituted or polysubstituted byhalogen or monosubstituted by (C₁ -C₃)alkoxy, Y is H, (C₁ -C₃)alkyl, (C₁-C₃)alkoxy or (C₁ -C₃)alkylthio, where the above-mentionedalkyl-containing radicals are unsubstituted or monosubstituted orpolysubstituted by halogen or monosubstituted or disubstituted by (C₁-C₃)alkoxy or (C₁ -C₃)alkylthio, or is a radical of the formula NR⁸ R⁹,(C₁ -C₆)-cycloalkyl, (C₂ -C₄)alkenyl, (C₂ -C₄)alkynyl, (C₃-C₄)alkenyloxy or (C₃ -C₄)alkynyloxy, Z is CH, R⁸ and R⁹ independentlyof one another are H, (C₁ -C₃)alkyl or (C₃ -C₄)alkenyl, X⁴ is CH₃, OCH₃,OC₂ H₅, CH₂ OCH₃ or Cl, Y⁴ CH₃, OCH₃, OC₂ H₅ or Cl.
 2. A compound asclaimed in claim 1, whereinW is an oxygen atom, n is the number zero andA is a radical of the formula ##STR79##
 3. A compound as claimed inclaim 1, whereinR² is H, (C₁ -C₃)alkyl, (C₁ -C₃)alkoxy, halogen or (C₁-C₃)alkylthio, and A is a radical of the formula ##STR80## in which Z isCH, X is halogen, (C₁ -C₂)alkyl, (C₁ -C₂)alkoxy, OCF₂ H, CF₃ or OCH₂ CF₃and Y is (C₁ -C₂)alkyl, (C₁ -C₂)alkoxy or OCF₂ H.
 4. The compound ofclaim 3 wherein R² is H, R³ is H, n is zero, W is 0,)and X and Y areeach --OCH₃.
 5. A herbicide or plant growth-regulating composition,which comprises a herbicidally or growth-regulatingly effective amountof a compound of the formula (I) or its salts as defined by claim 1 andformulation auxiliaries.
 6. A method of combating undesired plants or ofregulating the growth of plants, comprising applying an amount of acompound of the formula (I) or its salts as defined by claim 1, which isherbicidally effective or effective for regulating the growth of plantsto the plants, plant seed or a cultivated area.